What if the decision you are avoiding right now is the exact one that changes everything?
In this special crossover episode between the Edge of Excellence and The Entrepreneurial CEO, Matt Stewart sits down with Nicole McMackin and Michael Caito for a candid, funny, and surprisingly deep conversation about the handful of choices that shaped their careers, relationships, and lives. From walking away from law school to moving across the country with no guarantees, they unpack what bold decisions really feel like in the moment, and why waiting for certainty is usually the fastest way to stay stuck.
This episode dives into confidence, readiness, self-advocacy, risk, and the hidden power of choosing movement over perfection. Listen now if you are stuck in indecision, second-guessing your next move, or waiting to feel “ready.” This episode gives you rare, honest perspective from three leaders who know exactly what happens when you bet on yourself, and what it costs when you do not.
Timestamped Highlights
- [00:00] – Total honesty: what happens when you risk it all (and how Nicole frames life-changing decisions)
- [00:04] Nicole reveals the unexpected fork in the road that pulled her away from law school and into entrepreneurship.
- [00:08] Michael shares the cross-country move that changed his future, and why sometimes a physical move becomes a personal breakthrough.
- [00:13] The group tackles the decision that can elevate your life or quietly destroy it, choosing the right partner.
- [00:21] Nicole breaks down why so many talented professionals stay stuck, not because they lack skill, but because they never advocate for themselves.
- [00:27] Confidence versus competence, the honest truth about taking roles before you feel ready.
- [00:31] What big decisions actually feel like in real time, relief, fear, excitement, and the pressure to move before certainty arrives.
- [00:36] Each guest shares their personal framework for making tough calls when the stakes are high.
About The Guest
Nicole McMackin is President of Irvine Technology Corporation and the host of Elevate Your Career. She is known for combining executive leadership, career advocacy, and practical coaching, especially for women navigating growth in technology and leadership.
🔗 LinkedIn | Website
Michael Caito is CEO of Management Action Programs, Inc. (MAP) and former co-founder of Restaurants on the Run, one of the early restaurant delivery businesses later sold to Grubhub. He is known for his no-nonsense approach to accountability, leadership, and scaling businesses with discipline.
🔗 LinkedIn | Website
Mentioned Resources
- Choose Your Own Adventure books
- YPO (Young Presidents’ Organization)
- EO (Entrepreneurs’ Organization)
- Fortaleza (Las Abuelos) Tequila
- Big Canyon Country Club
- UCLA Women In Leadership Program
- Laura Schwab
- Greg Hughes
- CollegeWorks Painting
- State Street
- Emerging Leaders program
Important Links
- Grow, do great work, and lead the way: National Services Group (NSG)
- Join our Student Professional Program: Internship Application
- Connect with Matt on LinkedIn
- Watch full interviews on YouTube
The Edge of Excellence is an original podcast hosted by Matthew Stewart. Brought to you by College Works. Production and editing by Podcast Your Brand.